Novel cytotoxic oxygenated C29 sterols from the Colombian marine sponge Polymastia tenax

J Nat Prod. 2002 Aug;65(8):1161-4. doi: 10.1021/np0200459.

Abstract

Three new sterols, 5alpha,6alpha-epoxy-24R-ethylcholest-8(14)-en-3beta,7alpha-diol (1), 5alpha,6alpha-epoxy-24R-ethylcholest-8-en-3beta,7alpha-diol (2), and 3beta-hydroxy-24R-ethylcholesta-5,8-dien-7-one (3), have been isolated from the marine sponge Polymastia tenax, collected in the Colombian Caribbean, and their structures established on the basis of extensive NMR and MS studies. Compounds 1 and 2 showed antiproliferative activity toward A-549, HT-29, H-116, MS-1, and PC-3 tumor cells in the range 0.5-10 microg/mL.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Caribbean Region
  • Chromatography, High Pressure Liquid
  • Colombia
  • Colonic Neoplasms
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Lung Neoplasms
  • Male
  • Mass Spectrometry
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Porifera / chemistry*
  • Prostatic Neoplasms
  • Stereoisomerism
  • Sterols / chemistry
  • Sterols / isolation & purification*
  • Sterols / pharmacology
  • Tumor Cells, Cultured / drug effects
  • Tumor Cells, Cultured / enzymology
  • Tumor Cells, Cultured / metabolism

Substances

  • 3beta-hydroxy-24R-ethylcholesta-5,8-dien-7-one
  • 5alpha,6alpha-epoxy-24R-ethylcholest-8(14)-en-3beta,7alpha-diol
  • 5alpha,6alpha-epoxy-24R-ethylcholest-8-en-3beta,7alpha-diol
  • Sterols